Best Late Night TV Sports Moments

Late night television is at its best when a guest—especially someone unexpected—let’s his guard down and turns a run-of-the-mill interview into a hilarious and candid moment.

A close runner-up happens when hosts like Jimmy Fallon or Conan O’Brien use a bit to skewer the most current and absurd elements of pop culture—often with an assist from celebrities who know how not to take themselves too seriously.

Fortunately for sports fans, athletes and headline-grabbing sports-related news are frequently a huge part of these awesome late-night shenanigans.

Here are some of the best late night sports moments of the last few years.

Late Night Superlatives: Bengals-Steelers

Last season Jimmy Fallon did superlatives for every Monday Night Football game of the season. The segment, which is always pretty funny, basically takes official NFL photos from players and assigns them a high school yearbook-esque superlative based on them.

LA Kings Forward Dustin Penner’s Conan Internship

Because of the NHL lockout, Kings forward Dustin Penner found himself with a little extra time on his hands in December 2012. That gave him the opportunity to “intern” at the Conan offices. And by “intern,” obviously I mean intimidate and threaten anyone who asks him to do something or is unfortunate enough to pass him in the hall.

Clash of the Titus: Metta World Peace

Jimmy Kimmel knows as well as anyone that former Laker Metta World Peace is almost always a great recipe for hilarity—sometimes on purpose, other times inadvertently. Last year Kimmel had MWP on the show to compete against two-year-old Internet sensation Titus Ashby in a free-throw competition.

Marlon Wayans Wants Ronda Rousey to Dominate Him

Conan asked Marlon Wayans about his crush on UFC fighter Ronda Rousey on his recent appearance. Apparently, Wayans had tweeted something about wanted to smell Rousey’s hand and feet wraps at some point, and he looked a little bit ashamed of himself when Conan broached the subject.

Questions and Danswers: NFL Draft

Jimmy Fallon doesn’t subject people who want to be on TV to quite the same level of mockery that Jimmy Kimmel does, but he does let people be stupid on their own terms for the opportunity. In “Questions and Danswers,” people on the street are made to dance while discussing a certain topic, in this case the NFL draft.

Mark Cuban on Bud Selig, Alex Rodriguez

Never one to bite his tongue, Mark Cuban had some very blunt words for MLB commissioner Bud Selig and his treatment of Alex Rodriguez while talking to Jay Leno last summer. Cuban referred to the league as “Bud Selig’s mafia” and acknowledged his statement isn’t likely to ever improve his chances of buying a baseball team.

Derek Jeter At-Bat Songs

Last summer Jimmy Fallon welcomed Derek Jeter to the show and offered up a few homemade options for new at-bat songs for his favorite player. Jeter walked out to the songs, each more ridiculous than the last and serenaded by Fallon with music provided by The Roots.

Fake Mascots Who Should Never Dunk

This is a recurring segment that Conan does in which inexplicably weird (and obviously fake) mascots demonstrate that they should never dunk by attempting to dunk. It’s been going on for years now, and I don’t think there’s ever been a successful dunk.

Lie Witness News: Lakers in the Finals

“Lie Witness News” is a regular segment in which Jimmy Kimmel highlights people whose desire to be on television far outweighs any shame they have for being uninformed. Last summer the show took to the streets to ask people in Los Angeles how they felt about the Lakers playing in the NFL Finals. The fact that they weren’t playing in the finals was not much of a concern.

Jimmy Fallon and “Michael Jordan” Sing

In one of the weirder segments Jimmy Fallon ever had on late night, former SNL star Kristen Wiig appeared dressed...sorta...as NBA legend Michael Jordan. They improvised a bit about “Michael Jordan the singer” in which Wiig composed “the song Jordan is known for always singing” on the fly. It was equal parts weird and amazing. Amazingly weird.

Charles Barkley on Brett Favre

A few years ago David Letterman asked Charles Barkley about the infamous Brett Favre scandal that rocked the sports world, and Sir Charles inadvertently may have revealed some unpleasant details about his own high school experience.

Shaq Loses a Bet, Wears Tiny Pink Panties

Say what you will about Shaquille O’Neal, but the guy doesn’t welsh on a bet. After losing a bet he made with Jimmy Fallon, Shaq appeared on the show (post-Super Bowl) wearing a pair of hot pink panties that leave nothing to the imagination.

Skype Scavenger Hunt: NBA Edition

“Skype Scavenger Hunt” is a regular Jimmy Kimmel segment that is normally played by no-name viewers who are sent running frantically through their homes in search of various items. Occasionally he gets slightly bigger names to compete, like Rudy Gay and Kris Humphries, for instance.

#KentuckyDerbyRap

Hashtags is a segment Jimmy Fallon has had on his show forever, starting way back with Late Night. Each week he announces a hashtag and allows fans to submit theirs, with a few being read on the show. Recently it was #KentuckyDerbyRap, and submissions included “I got my fancy hat and I’m rockin’ seersucker, drinkin’ mint juleps while you’re drinkin’ beer, sucker!” and were sung by The Roots.

The History of the Super Bowl

Maybe it’s because he’s been planning for retirement for a while, but David Letterman’s comedy bits have been far more miss than hit in recent years. But last January NFL historian Jeff Tolnick appeared to sing “The History of the Super Bowl,” which was so amazingly stupid that it actually really worked.

Guillermo at NBA Finals Media Day

Guillermo is Jimmy Kimmel’s diminutive sidekick, and last year he was sent to interview the players at the NBA Finals media day. He asks the players hilariously inane questions and is completely shut down by LeBron James, who ignores Guillermo screaming his name an epic 51 times.

From the Vault: U.S. Open Ball Boy Tryouts

Early in the show’s run, Jimmy Fallon and announcer/sidekick Steve Higgins were both put through the ringer during a ball boy tryout for the U.S. Open. They were at least 20 years older than the other competitors and spent most of the time menacing each other. These two don’t get out of the studio much, but this will make you wish they did.

NBA Press Conference Fashion Is Getting Insane

NBA players definitely take more fashion risks than other athletes, with many saving their most outrageous duds for the playoffs. A few years ago Conan put together a highlight reel of their most adventurous looks. I’m surprised the beekeeper suit hasn’t taken off yet—Russell Westbrook would rock the hell out of that.

Matt Harvey Fools Mets Fans

It’s always funny to see people speak with authority about something they aren’t necessarily an authority on. During last year’s All-Star event in New York, Jimmy Fallon sent Mets pitcher Matt Harvey to the streets to ask people what they thought about Mets pitcher Matt Harvey. The results were predictably hilarious.

Kobe Bryant on Phil Jackson and Michael Jordan

Lakers great Kobe Bryant doesn’t do many media appearances outside of addressing reporters during the NBA season, but he should. He is always refreshingly blunt and honest, like when he recently talked to Jimmy Kimmel about Phil Jackson’s penchant for creative storytelling and the time he told Michael Jordan he’d kick his ass one-on-one.

Jon Dore Finds a Superior Basketball League

During the NBA lockout, comedian Jon Dore stopped by to talk to Conan about his frustration with the league and debut a fantastic video of a superior basketball league. The better league was a kids league, and Dore talked to them about the price of tickets, love of the game, height advantages and league harmony between their players and commissioner.

Can You Name a College Basketball Player?

Jimmy Kimmel does variations of this bit all the time, basically to prove people will say or do anything to be on TV. In March he asked supposed college basketball fans if they were enjoying March Madness and then asked them to name a single college basketball player. Most of them could not.

NFL Replacement Ref Highlight Reel

The NFL replacement referees who officiated the first few games of the 2012 season were an abject disaster for the league. They were comically bad enough that Conan’s hyperbolic depiction of them doesn’t feel that exaggerated in retrospect.

Puppies Predict the Super Bowl

Jimmy Fallon has found the absolute best way to predict pretty much everything: puppies. It doesn’t matter if they’re right or wrong, because they’re always ridiculously adorable. In January they predicted the Broncos would best the Seahawks in the Super Bowl, but just try to stay mad at those little faces.

Rich Eisen Sums Up the NFL Draft

Recently, NFL Network’s Rich Eisen spoke with Seth Meyers about, among other things, the odd appeal of the draft. “It’s just basically names being read out at a podium every 10 minutes.” As someone who was glued to the television for three straight days, that assessment makes me feel like...kind of an idiot. Yay!

Egg Russian Roulette with David Beckham

Egg Russian roulette is one of the funniest recurring bits Jimmy Fallon has done. The premise is that he and a celebrity, in this case soccer star David Beckham, sit down with a dozen eggs—half of which are hardboiled. Then they take turns smashing them against their foreheads as Steve Higgins provides epic commentary inspired by The Deer Hunter.

People React to Donald Sterling’s NAACP Award

When audio leaked of Clippers owner Donald Sterling saying unforgivably racist things, he was due to receive a second lifetime achievement award from the Los Angeles NAACP. Obviously that was cancelled, and Sterling received a lifetime ban from the NBA. The story was mighty big news nationally, but Jimmy Kimmel still found plenty of clueless people on the streets of LA who were eager to congratulate Sterling for a job well done.

Shaq and Jimmy Fallon Exchange Jackets

Chris Farley first demonstrated the hilarity of improperly sized clothing with his “Fat Guy in a Little Coat” bit in Tommy Boy. Jimmy Fallon proved it’s almost as funny going the other way, when he tried on Shaquille O’Neal’s stunningly large suit jacket. Shaq didn’t even bother trying to squeeze into Fallon’s tiny duds.

Key and Peele's Ridiculous Football Names

The ridiculous football names sketch has been one of Key & Peele’s most popular throughout the series run. Last year they did a preview for the upcoming season on Conan and talked about the pressure to top the ridiculousness each year. In addition to “Bismo Funyuns,” “Quiznatodd Bidness” and “Quackadilly Blip,” they added a bonus player at the end that didn’t seem all that out of place.

The JKL Children’s Choir Presents NBA Tweets

A delightful variation of “Mean Tweets,” last summer Jimmy Kimmel had members of the JKL Children’s Choir sing tweets composed by various NBA players. The tweet in this video is Roy Hibbert’s: “I was in a cab on the way 2dinner 2night. As i get out I see a girl calmly taking a poop on the side of the road!” That one is my personal favorite, but the rest are worth a watch.

Evolution of End-Zone Dancing

Jimmy Fallon and Justin Timberlake always make magic together. They’ve been great on Saturday Night Live over the years, and their "History of Rap" installments are always viral hits. The "Evolution of End-Zone Dancing" bit they did together was yet another home run...or touchdown.

Charles Barkley Is Tired of Shaq Picking on Him

Charles Barkley is every host's dream because he is physically incapable of filtering himself and has an incredible sense of humor. Recently, he stopped by and talked to Conan about an unpleasantly revealing photo of him that Shaquille O’Neal posted to Instagram. Sir Charles also commented on the pair’s rivalry, Shaq’s billion endorsements and his theory about how Shaq gets into those cars to shoot Buick commercials.

Robinson Cano Surprises Yankees Fans

Anyone who thinks that Yankees fans talk a big game but can’t really back it up was given the ultimate gift by Jimmy Fallon recently. Fans in New York were given the opportunity to talk trash to a cardboard cutout of Robinson Cano, who was making his first return as a member of the Mariners. Watch Cano himself pop out from behind the photo and see Yanks fans immediately change their tone.

Bob Costas’ Eye Infection Is Getting Bad

Looking back on it, the increasingly grisly eye infection of NBC’s Bob Costas may have been the biggest ongoing story of the Sochi Olympics—at least in the U.S. In February Conan tracked the development of the world’s most famous eye infection. He may have taken some liberties, but this is pretty much how I remember it happening.

Epic #SochiFail: Wolf in My Hall

Jimmy Kimmel has had some success with pranking a gullible public. First with his “Worst Twerk Fail EVER,” then again with “Epic #SochiFail: Wolf in My Hall Prank.” He capitalized on #SochiProblems mania by conspiring with American Olympian Kate Hansen to convince the world wolves were wandering the hallways of the athlete dormitories. Kimmel must have been delighted when the story was picked up and reported on as fact.

Nip Syncing

Football-player-turned-actor Terry Crews is well-known for his ability to...uh...make his pecs bounce? I guess that’s the best way to say that. Recently, he and Jimmy Fallon did a shirtless “nip syncing” duet to the Stevie Wonder classic “Ebony and Ivory.” It was 50 shades of glorious.

Mean Tweets: NBA Edition

Jimmy Kimmel caught lightning in a bottle with his “Mean Tweets” bit. Having celebrities read the hilariously nasty things strangers say about them on Twitter is perfect in its simplicity. The NBA edition was particularly fantastic—they should have just had Bill Simmons read tweets about himself for the full hour.